1-[(E)-(2-Methyl-3-nitro­phen­yl)imino­meth­yl]-2-naphthol

Bingöl Alpaslan, Y.; Alaman Ağar, A.; Işık, Ş.

doi:10.1107/S1600536810043461

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3052

https://doi.org/10.1107/S1600536810043461

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1-[(E)-(2-Methyl-3-nitrophenyl)iminomethyl]-2-naphthol

Yelda Bingöl Alpaslan,^a ^* Ayşen Alaman Ağar ^b and Şamil Işık ^a

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit-Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: ybingol@omu.edu.tr

(Received 23 October 2010; accepted 25 October 2010; online 6 November 2010)

The title Schiff base compound, C₁₈H₁₄N₂O₃, has an intermediate state between NH and OH tautomers. The molecular structure is stabilized by an O—H⋯N hydrogen bond. The dihedral angle between the naphthalene ring system and the benzene ring is 37.44 (5)°.

Related literature

For the biological properties of Schiff bases, see: Lozier et al. (1975 ). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009 ); Yeap et al. (2009 ). For Schiff base tautomerism, see: Hökelek et al. (2000 ); Karabıyık et al. (2007 ); Odabaşoğlu et al. (2005 ); Kılıç et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₄N₂O₃
M_r = 306.31
Monoclinic, P 2₁ /c
a = 12.5520 (9) Å
b = 7.4731 (4) Å
c = 15.8610 (13) Å
β = 90.806 (6)°
V = 1487.65 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.7 × 0.47 × 0.12 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.989, T_max = 0.997
9684 measured reflections
3088 independent reflections
1969 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.153
S = 0.94
3088 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.10 (3)	1.48 (3)	2.5310 (19)	159 (3)

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810043461/bt5391sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043461/bt5391Isup2.hkl

checkCIF report

Comment top

Schiff bases often exhibit various biological activities and in many cases were shown to have antibacterial, anticancer, anti-inflammatory and antitoxic properties (Lozier et al., 1975). Schiff bases have also been used as versatile ligands in coordination chemistry (Kargar et al., 2009; Yeap et al., 2009). There are two types of intramolecular hydrogen bonds in Schiff bases, namely N—H···O in keto (NH) (Hökelek et al., 2000) and N···H—O in enol (OH) (Odabaşoǧlu et al., 2005) tautomeric forms. Our investigations shows that in the title compound is described as an intermediate state between NH and OH tautomers. An ORTEP-3 (Farrugia, 1997) plot of the molecule of (I) is shown in Fig.1. The C2—O1 [1.331 (2) Å] and C11—N1 [1.299 (2) Å] bond lengths are intermediate between the single and double C—O (1.362 and 1.222 Å, respectively) and C—N bond lengths (1.339 and 1.279 Å, respectively) (Allen et al., 1987). The molecular structure is stabilized by an intramolecular O—H···N hydrogen bond. It is a well known fact that H atoms participating in intramolecular hydrogen bonds in Schiff bases are rather mobile. The molecule can be regarded as having an intermediate state between its canonical OH and NH forms, and therefore the O1—H1 bond [1.10 (3) Å] remains somewhat longer than its expected value (Karabıyık et al., 2007). Similar results were observed for 2-[(4-Methoxyphenyl)iminomethyl]-4- nitrophenol (Kılıç et al., 2009). The molecule of the title compound is not planar, with a dihedral angle of 37.44 (5)° between naphthalene and benzene rings.

Related literature top

For the biological properties of Schiff bases, see: Lozier et al. (1975). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009); Yeap et al. (2009). For Schiff base tautomerism, see: Hökelek et al. (2000); Karabıyık et al. (2007); Odabaşoǧlu et al. (2005); Kılıç et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by refluxing a mixture of a solution containing 2-hydroxy-1-naphthaldehyde (172 mg, 0,0986 mmol) in ethanol (30 ml) and a solution containing 2-methyl-3-nitroaniline (15 mg, 0,0986 mmol) in ethanol (30 ml. The reaction mixture was stirred for 1 h under reflux. Single crystals of the title compound for x-ray analysis were obtained by slow evaporation of an ethanol solution (Yield 68%; m.p. 428–432 K).

Structure description top

For the biological properties of Schiff bases, see: Lozier et al. (1975). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009); Yeap et al. (2009). For Schiff base tautomerism, see: Hökelek et al. (2000); Karabıyık et al. (2007); Odabaşoǧlu et al. (2005); Kılıç et al. (2009). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

1-[(E)-(2-Methyl-3-nitrophenyl)iminomethyl]-2-naphthol top

Crystal data top

C₁₈H₁₄N₂O₃	F(000) = 640
M_r = 306.31	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8237 reflections
a = 12.5520 (9) Å	θ = 1.3–27.3°
b = 7.4731 (4) Å	µ = 0.10 mm⁻¹
c = 15.8610 (13) Å	T = 296 K
β = 90.806 (6)°	PRISM., yellow
V = 1487.65 (18) Å³	0.7 × 0.47 × 0.12 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	3088 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.6°
ω scans	h = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
T_min = 0.989, T_max = 0.997	l = −19→17
9684 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.095P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
3088 reflections	Δρ_max = 0.24 e Å⁻³
213 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

Crystal data top

C₁₈H₁₄N₂O₃	V = 1487.65 (18) Å³
M_r = 306.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.5520 (9) Å	µ = 0.10 mm⁻¹
b = 7.4731 (4) Å	T = 296 K
c = 15.8610 (13) Å	0.7 × 0.47 × 0.12 mm
β = 90.806 (6)°

Data collection top

Stoe IPDS II diffractometer	3088 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1969 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.997	R_int = 0.061
9684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.24 e Å⁻³
3088 reflections	Δρ_min = −0.19 e Å⁻³
213 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.41741 (13)	0.0570 (2)	0.21696 (11)	0.0439 (4)
C2	0.35899 (13)	0.0014 (2)	0.28723 (11)	0.0489 (4)
C3	0.24646 (15)	−0.0112 (3)	0.28256 (13)	0.0605 (5)
H3	0.2085	−0.0498	0.3291	0.073*
C4	0.19459 (14)	0.0329 (3)	0.21045 (13)	0.0627 (5)
H4	0.1206	0.0258	0.2086	0.075*
C5	0.24883 (13)	0.0898 (3)	0.13724 (12)	0.0510 (4)
C6	0.19243 (15)	0.1360 (3)	0.06252 (14)	0.0618 (5)
H6	0.1184	0.1309	0.0616	0.074*
C7	0.24441 (16)	0.1873 (3)	−0.00749 (14)	0.0648 (5)
H7	0.2062	0.2181	−0.0560	0.078*
C8	0.35511 (16)	0.1941 (3)	−0.00694 (13)	0.0606 (5)
H8	0.3907	0.2270	−0.0556	0.073*
C9	0.41227 (14)	0.1526 (3)	0.06482 (11)	0.0515 (5)
H9	0.4862	0.1594	0.0642	0.062*
C10	0.36138 (12)	0.1001 (2)	0.13924 (11)	0.0441 (4)
C11	0.53047 (13)	0.0720 (2)	0.22409 (12)	0.0471 (4)
H11	0.5686	0.1078	0.1772	0.057*
C12	0.69421 (13)	0.0479 (2)	0.29892 (11)	0.0487 (4)
C13	0.74005 (13)	0.1057 (2)	0.37579 (11)	0.0461 (4)
C14	0.85070 (14)	0.1110 (3)	0.37726 (12)	0.0557 (5)
C15	0.91392 (15)	0.0627 (4)	0.31127 (15)	0.0757 (7)
H15	0.9877	0.0702	0.3159	0.091*
C16	0.86568 (16)	0.0027 (4)	0.23779 (15)	0.0813 (7)
H16	0.9068	−0.0323	0.1924	0.098*
C17	0.75641 (15)	−0.0048 (3)	0.23229 (13)	0.0655 (6)
H17	0.7239	−0.0461	0.1830	0.079*
C18	0.67164 (14)	0.1657 (3)	0.44710 (12)	0.0562 (5)
H18A	0.7161	0.2005	0.4940	0.084*
H18B	0.6260	0.0692	0.4637	0.084*
H18C	0.6290	0.2657	0.4292	0.084*
N1	0.58208 (11)	0.0375 (2)	0.29377 (9)	0.0481 (4)
N2	0.90826 (13)	0.1746 (3)	0.45348 (12)	0.0695 (5)
O1	0.40602 (11)	−0.0411 (2)	0.36024 (8)	0.0609 (4)
O2	0.88124 (15)	0.1224 (3)	0.52187 (11)	0.1036 (7)
O3	0.98286 (12)	0.2763 (3)	0.44235 (12)	0.0997 (6)
H1	0.489 (3)	−0.023 (4)	0.343 (2)	0.128 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0467 (8)	0.0410 (9)	0.0437 (9)	0.0020 (7)	−0.0038 (7)	−0.0022 (8)
C2	0.0532 (9)	0.0499 (10)	0.0435 (10)	0.0026 (7)	0.0003 (7)	−0.0048 (8)
C3	0.0548 (10)	0.0759 (14)	0.0510 (11)	−0.0020 (9)	0.0092 (8)	−0.0036 (10)
C4	0.0419 (9)	0.0810 (14)	0.0652 (13)	0.0029 (9)	0.0014 (9)	−0.0089 (11)
C5	0.0472 (9)	0.0541 (11)	0.0515 (11)	0.0041 (7)	−0.0059 (8)	−0.0083 (9)
C6	0.0506 (10)	0.0709 (13)	0.0634 (13)	0.0104 (9)	−0.0158 (9)	−0.0083 (11)
C7	0.0716 (12)	0.0672 (13)	0.0552 (12)	0.0102 (10)	−0.0218 (10)	−0.0007 (10)
C8	0.0738 (12)	0.0603 (12)	0.0474 (11)	−0.0026 (9)	−0.0073 (9)	0.0052 (9)
C9	0.0531 (9)	0.0517 (10)	0.0496 (11)	−0.0050 (8)	−0.0061 (8)	0.0033 (9)
C10	0.0478 (9)	0.0391 (9)	0.0453 (9)	0.0011 (7)	−0.0044 (7)	−0.0029 (7)
C11	0.0493 (9)	0.0461 (10)	0.0459 (10)	−0.0011 (7)	−0.0026 (7)	0.0003 (8)
C12	0.0470 (9)	0.0509 (10)	0.0480 (10)	0.0015 (7)	−0.0048 (7)	−0.0003 (8)
C13	0.0473 (8)	0.0476 (10)	0.0434 (9)	−0.0002 (7)	−0.0050 (7)	0.0031 (8)
C14	0.0487 (9)	0.0655 (12)	0.0526 (11)	0.0008 (8)	−0.0113 (8)	−0.0018 (9)
C15	0.0443 (10)	0.1099 (19)	0.0727 (15)	0.0034 (10)	−0.0026 (9)	−0.0122 (14)
C16	0.0546 (11)	0.122 (2)	0.0674 (14)	0.0087 (12)	0.0058 (10)	−0.0223 (15)
C17	0.0570 (10)	0.0860 (15)	0.0533 (12)	0.0069 (10)	−0.0049 (9)	−0.0168 (11)
C18	0.0567 (10)	0.0636 (12)	0.0481 (10)	−0.0007 (8)	−0.0018 (8)	0.0019 (9)
N1	0.0471 (8)	0.0497 (8)	0.0473 (8)	0.0010 (6)	−0.0083 (6)	−0.0003 (7)
N2	0.0517 (9)	0.0915 (14)	0.0646 (12)	0.0002 (9)	−0.0173 (8)	−0.0044 (11)
O1	0.0635 (8)	0.0769 (10)	0.0422 (7)	0.0031 (7)	−0.0009 (6)	0.0051 (7)
O2	0.1009 (13)	0.154 (2)	0.0552 (10)	−0.0192 (12)	−0.0220 (9)	0.0058 (11)
O3	0.0650 (9)	0.1341 (17)	0.0991 (13)	−0.0299 (10)	−0.0239 (9)	−0.0091 (12)

Geometric parameters (Å, º) top

C1—C2	1.406 (2)	C11—H11	0.9300
C1—C11	1.426 (2)	C12—C17	1.380 (3)
C1—C10	1.447 (2)	C12—C13	1.409 (2)
C2—O1	1.331 (2)	C12—N1	1.411 (2)
C2—C3	1.417 (3)	C13—C14	1.389 (2)
C3—C4	1.349 (3)	C13—C18	1.498 (3)
C3—H3	0.9300	C14—C15	1.371 (3)
C4—C5	1.420 (3)	C14—N2	1.478 (3)
C4—H4	0.9300	C15—C16	1.381 (3)
C5—C6	1.415 (3)	C15—H15	0.9300
C5—C10	1.415 (2)	C16—C17	1.374 (3)
C6—C7	1.351 (3)	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.390 (3)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.372 (3)	C18—H18C	0.9600
C8—H8	0.9300	N2—O2	1.206 (2)
C9—C10	1.406 (2)	N2—O3	1.221 (2)
C9—H9	0.9300	O1—H1	1.10 (3)
C11—N1	1.299 (2)

C2—C1—C11	119.33 (16)	C1—C11—H11	118.8
C2—C1—C10	119.26 (15)	C17—C12—C13	121.45 (16)
C11—C1—C10	121.41 (15)	C17—C12—N1	120.96 (16)
O1—C2—C1	122.05 (15)	C13—C12—N1	117.52 (15)
O1—C2—C3	117.35 (16)	C14—C13—C12	114.78 (16)
C1—C2—C3	120.60 (16)	C14—C13—C18	124.22 (16)
C4—C3—C2	119.81 (18)	C12—C13—C18	120.91 (15)
C4—C3—H3	120.1	C15—C14—C13	124.69 (17)
C2—C3—H3	120.1	C15—C14—N2	115.32 (16)
C3—C4—C5	122.38 (17)	C13—C14—N2	119.98 (17)
C3—C4—H4	118.8	C14—C15—C16	118.58 (18)
C5—C4—H4	118.8	C14—C15—H15	120.7
C6—C5—C10	119.57 (18)	C16—C15—H15	120.7
C6—C5—C4	121.22 (16)	C17—C16—C15	119.5 (2)
C10—C5—C4	119.21 (16)	C17—C16—H16	120.3
C7—C6—C5	121.06 (17)	C15—C16—H16	120.3
C7—C6—H6	119.5	C16—C17—C12	120.96 (19)
C5—C6—H6	119.5	C16—C17—H17	119.5
C6—C7—C8	119.95 (17)	C12—C17—H17	119.5
C6—C7—H7	120.0	C13—C18—H18A	109.5
C8—C7—H7	120.0	C13—C18—H18B	109.5
C9—C8—C7	120.52 (19)	H18A—C18—H18B	109.5
C9—C8—H8	119.7	C13—C18—H18C	109.5
C7—C8—H8	119.7	H18A—C18—H18C	109.5
C8—C9—C10	121.39 (17)	H18B—C18—H18C	109.5
C8—C9—H9	119.3	C11—N1—C12	121.57 (15)
C10—C9—H9	119.3	C11—N1—H1	97.0 (12)
C9—C10—C5	117.49 (16)	C12—N1—H1	141.0 (12)
C9—C10—C1	123.80 (15)	O2—N2—O3	123.89 (19)
C5—C10—C1	118.71 (16)	O2—N2—C14	119.41 (19)
N1—C11—C1	122.38 (17)	O3—N2—C14	116.68 (19)
N1—C11—H11	118.8	C2—O1—H1	99.5 (17)

C11—C1—C2—O1	−1.2 (3)	C2—C1—C11—N1	−0.6 (3)
C10—C1—C2—O1	179.59 (16)	C10—C1—C11—N1	178.56 (17)
C11—C1—C2—C3	178.70 (17)	C17—C12—C13—C14	2.2 (3)
C10—C1—C2—C3	−0.5 (3)	N1—C12—C13—C14	179.22 (16)
O1—C2—C3—C4	178.99 (19)	C17—C12—C13—C18	178.92 (19)
C1—C2—C3—C4	−0.9 (3)	N1—C12—C13—C18	−4.1 (3)
C2—C3—C4—C5	1.0 (3)	C12—C13—C14—C15	−0.9 (3)
C3—C4—C5—C6	−179.8 (2)	C18—C13—C14—C15	−177.5 (2)
C3—C4—C5—C10	0.4 (3)	C12—C13—C14—N2	178.16 (18)
C10—C5—C6—C7	1.0 (3)	C18—C13—C14—N2	1.6 (3)
C4—C5—C6—C7	−178.9 (2)	C13—C14—C15—C16	−0.6 (4)
C5—C6—C7—C8	0.5 (3)	N2—C14—C15—C16	−179.7 (2)
C6—C7—C8—C9	−1.4 (3)	C14—C15—C16—C17	0.8 (4)
C7—C8—C9—C10	0.8 (3)	C15—C16—C17—C12	0.5 (4)
C8—C9—C10—C5	0.6 (3)	C13—C12—C17—C16	−2.1 (3)
C8—C9—C10—C1	−179.21 (17)	N1—C12—C17—C16	−179.0 (2)
C6—C5—C10—C9	−1.5 (3)	C1—C11—N1—C12	178.07 (15)
C4—C5—C10—C9	178.39 (18)	C17—C12—N1—C11	−37.0 (3)
C6—C5—C10—C1	178.35 (17)	C13—C12—N1—C11	145.97 (18)
C4—C5—C10—C1	−1.8 (3)	C15—C14—N2—O2	−135.8 (2)
C2—C1—C10—C9	−178.35 (16)	C13—C14—N2—O2	45.0 (3)
C11—C1—C10—C9	2.5 (3)	C15—C14—N2—O3	42.8 (3)
C2—C1—C10—C5	1.8 (2)	C13—C14—N2—O3	−136.3 (2)
C11—C1—C10—C5	−177.34 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.10 (3)	1.48 (3)	2.5310 (19)	159 (3)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O₃
M_r	306.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.5520 (9), 7.4731 (4), 15.8610 (13)
β (°)	90.806 (6)
V (Å³)	1487.65 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.7 × 0.47 × 0.12

Data collection
Diffractometer	Stoe IPDS II
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.989, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	9684, 3088, 1969
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.153, 0.94
No. of reflections	3088
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.10 (3)	1.48 (3)	2.5310 (19)	159 (3)

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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